42206-94-0
Acetyl-trans-resveratrol
CAS: 42206-94-0
Molecular Formula: C20H18O6
42206-94-0 - Names and Identifiers
| Name | Acetyl-trans-resveratrol |
| Synonyms | AcetylResveratrol Acetyl Resveratrol Acetyl trans-resveratrol Acetyl-trans-resveratrol trans-Resveratrol Triacetate 3,5,4'-Tri-O-acetylresveratrol 3,4',5-Triacetoxy-trans-stilbene Acetyl-resveratrol, Acetyl Trans-resveratrol 4-[(E)-2-(3,5-Diacetoxyphenyl)vinyl]phenyl acetate 3-(acetyloxy)-5-{(E)-2-[4-(acetyloxy)phenyl]ethenyl}phenyl acetate (non-preferred name) trans-Triacetylresveratrol, trans-Resveratrol triacetate, 4-[(E)-2-(3,5-Diacetoxphenyl)vinyl]phenyl acetate |
| CAS | 42206-94-0 |
| EINECS | 695-560-1 |
| InChI | InChI=1/C20H18O6/c1-13(21)24-18-8-6-16(7-9-18)4-5-17-10-19(25-14(2)22)12-20(11-17)26-15(3)23/h4-12H,1-3H3/b5-4+ |
42206-94-0 - Physico-chemical Properties
| Molecular Formula | C20H18O6 |
| Molar Mass | 354.35 |
| Density | 1.241±0.06 g/cm3(Predicted) |
| Melting Point | 117.0 to 121.0 °C |
| Boling Point | 504.8±50.0 °C(Predicted) |
| Flash Point | 221.5°C |
| Solubility | DMSO : 125 mg/mL (352.76 mM; Need ultrasonic) |
| Vapor Presure | 2.57E-10mmHg at 25°C |
| Appearance | Powder |
| Color | white to tan |
| Storage Condition | room temp |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| Refractive Index | 1.599 |
| MDL | MFCD01546481 |
| In vitro study | Triacetylresveratrol significantly down-regulates anti-apoptotic Bcl-2 family protein Mcl-1 and up-regulates pro-apoptotic Bcl-2 family proteins Bim and Puma. Triacetylresveratrol inhibits cell viability, and induces apoptosis of pancreatic cancer cells in a concentration and incubation time-dependent manner. |
42206-94-0 - Risk and Safety
| Risk Codes | R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
42206-94-0 - Reference Information
| introduction | resveratrol is a phytoalexin found in grape skins, seeds and other plants. Resveratrol ester is considered to be a drug precursor of a metabolite. Derivatives with acyl chains will increase its affinity with the cell membrane, making it easier to pass through the cell membrane, and the esterase in the cell It can cut the ester bond, release resveratrol, and improve the bioavailability of resveratrol. The above shows that acetylation of resveratrol is of great significance. Acetylation to acetylated resveratrol increases its ability to pass through the phospholipid bilayer to improve the bioavailability of resveratrol. |
| appearance | acetylated resveratrol is white to white powder or crystalline. |
| mechanism of action | after acetylated resveratrol enters the body, it is converted into resveratrol in the body and exerts its biological activity. Compared with ordinary resveratrol, acetylated resveratrol has the following main characteristics: 1) The stability is enhanced. Because the three active phenolic hydroxyl groups are acetylated, the stability of acetylated resveratrol is significantly improved; 2) The bioavailability is improved. Due to the extension of the residence time in the body, the half-life is improved, and the bioavailability is better. Acetylated resveratrol can be widely used in food, beverage and health products. |
| application | since resveratrol is a polyhydroxyphenolic compound and is easy to be oxidized, after protecting the phenolic hydroxyl group with acetyl group, the obtained acetylated resveratrol is very stable in nature. at the same time, acetylated resveratrol, as a prodrug of resveratrol, helps to prolong the half-life of resveratrol and increase the bioavailability. |
| synthesis method | 1) using 3,4 ', 5-trimethoxystilbene as raw material, using the complex formed by aluminum trichloride and triethylamine as demethylation reagent, under the action of inorganic salts, resveratrol is obtained after demethylation reaction; 2) The resveratrol obtained in step 1) is acetylated with acetic anhydride under the action of triethylamine to obtain acetylated resveratrol. In the steps of the present invention, the reaction formula of the demethylation reaction is: |
| Biological activity | Triacetylresveratrol are Resveratrol acetylated analogs. Triacetylresveratrol reduced STAT3 and NF-κB phosphorylation. Has anti-cancer effects. |
Last Update：2024-04-09 20:52:54
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